
Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

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because difference of "generally" accepted good performance is right at the $200-300 level. The exceptions are known... The pair of FIIO FT1 and FT1 Pro, Philips SHP9600, Koss's 4 on ear "headphones", Grado SR60x, Sennheiser x Drop HD6xx (sale price) or even the HD58x...🤷🏻♂️ There's a reason why IEM is competitive with headphones at that under $300 price point. Price to performance...IEM usually perform better than headphones
Grado SR60X They pretty much cured my Gear Acquisition Syndrome. If you can get cans that sound that great for so little money, what is the point of chasing perfection?
as another glasses user I've had some offer surprisingly good comfort. Normally on-ears are a bad idea, but my grado sr60x are super comfortable *after I stretched out the headband*, you have to really stretch it out so that it applies almost no pressure to the ears, it's basically floating there, suspended only by the headband. Another is koss KSC75, again, usually having more stuff hooking to the ear is a bad idea, but I can wear these things all day long (which I have done before...). Sennheiser HD600 I was also expecting to suck, especially when I first put them on and felt how much pressure they apply. I still need to bend them a little more to relieve pressure, but even before stretching they applied more pressure near the jaw below the ear than my glasses frame. worth noting I have metal frames with wide (more like tall) but thin (1mm or less) temples, so I can get away with more pressure than frames with thick temples.
I’d be willing to be at least half of those who dog on Grados in here have never listened to a pair. Grado sr60xs are $100. Less if on sale (which they often are). The only reason these people don’t touch Grado is a stranger on the internet made fun of them. I’m actually not a fan of Grado—they sound great but I hate the way they fit—but I at least own a pair and am speaking from experience. Buy what you want. This sub tends to be very meme-y in its suggestions.
Ahh my two favourites are definitely grado sr60x and hifiman sundaras. Idk why but that treble in the grados is just so nice for so much of my music, and I really enjoy the super light on-ear feel. Then the sundaras are absolutely my most used headphones, by far. They are always at my desk and these days even next to my bed. If I’m being honest my sundaras don’t do anything that is particularly mind-blowing but I just love the sound so much. The build quality is terrible and the cable they came with got swapped out immediately alongside the pads, but the sound is just right. Honorable mentions go to kph40s which are the single comfiest headphones ever, I usually forget in even wearing them and they sound so ridiculously good for 30$ headphones. Then to hd660s which I keep at my desk as well, and since they are so easy to drive compared to hd600 and to my sundaras, I even used them out of my phone for years.
Get the Grado's. I have the basic SR60X and I'm really happy with them, and the higher models get even better.
Niche choice, but I'm extremely happy with my Grado's SR60X.
Yup, I can wear them entire day and not feel any discomfort.

Sennheiser
HD 560S
Budget gaming king with clear sound, but tight fit.

Sony
WH-1000XM4
ANC king, durable, but unreliable mic and touch controls.

Sennheiser
HD 6XX
Legendary mids, durable, but narrow soundstage and weak bass.

Sennheiser
HD 490 PRO
Super comfortable, wide soundstage for gaming, versatile pads.

Sennheiser
HD 599
Super comfortable, easy to drive, wide soundstage, open-back.

Ranked #1
Sennheiser - HD 6XX

Ranked #1
FiiO - FT1 Closed-back Headphones

Ranked #1
Sennheiser - HD 560S

Ranked #1
Sony - MDR-7506

Ranked #1
Sony - WH-1000XM4

Ranked #1
Sennheiser - HD 560S